I am using Illustrator CS 5 on a Mac Pro using Lion OS X. I am an intermediate user having had to move over from Freehand. I just started using the Pencil tool today but can't figure out how to activate the modifier keys to work with the Pencil tool. They work with all the other tools like shapes and the pen tool, just not with Pencil.

I did a web search and found several threads about similar problems that seemed to be concerned with the modifier keys not working with ALL command. Suggestions included turning off Foxfire, Outlook, Entourage, etc. with indifferent success. Also deleting the preferences files. But I only have a problem with one command. I have found tutorials that indicate using the modifier keys with Pencil so I know it is supposed to work. Is there a solution? I don't know a lot about this so please be explicit in any replys. I am not an IT expert and didn't follow the jargon in most of the posts I found.

I have been working in Photoshop and you can hold down the shift key to constrain the pencil tool to draw a straight line. I was hoping to use the same tool in Illustrator to create a more hand drawn look. As I am new to Illustrator I am still learning the capabilities of the program. I have come to realize that Illustrator doesn't have the same Filter options that Photoshop has. I wanted to be able to draw over a computer rendered plan to make it look looser and thought using Illustrator would give me more editing options, Photoshop is pretty limited in this.

So I was hoping to be able to change the appearance of a drawn line using Pencil, and the shift key to keep the lines straight. I don't believe this is feasible in Illustrator, I have seen some references to using Active Trace but can't figure out how to use it or if it would even work. What I really need is a program that will "Jitter" the lines to appear drawn with a felt pen or marker.

I don't know of any constraints possible for the pencil tool in Illustrator.

If you double click on the pencil tool in the toolbox you have some options to control how the pencil works, just play with them and you will figure it out.

The way I use it for things that you describe, I start with loose drawing of the paths with the option to stay selected. This allows me to change or refine the paths as desired by drawing again over sections of the selected path with the pencil or when holding Alt key it turns into the smoothing pencil.

For the straight segments, when creating the path, I try to draw it so it passes through the starting and ending points of the intended straight segment but without any effort to keep it straight. When I finish drawing the entire path, I take the lasso tool (Q), select the redundant points on the intended straight segments and remove them (not delete) by using a hotkey made for the remove points button on the property bars. Then if necessary use the Convert anchor point tool (Shift + C) to turn into corner points the first and last anchor points of the straight segments by clicking on the handles and snapping them into their points.

Conversely.. with the Pen tool in use Option/Alt + Shift to temporarily switch to the Pencil Tool (and keep path/anchor active)

My goal would be to draw either beziers or free form without the need to switch tools. In addition, there's no way to dynamically join a Pen-drawn path with a Pencil-drawn path. You have to select endpoints and join them.

if you double click the pencil tool, you can set pencil tool options as well (smoothness, fidelity etc). And with the pencil tool selected by pressing and holding the option key, the tool changes to the smoothness tool to refine your line..

... I would like to see some constraint capability with the pencil tool. It's available with the brush tool, why not the pencil tool?

It should be much better than that and they should improve the brush tool too by making the constraint work in the middle of a freehand stroke. Currently it is either straight lines or freehand. Also in addition to the angle constraints they should make these tools Pencil, Brush, and even the Lasso selection tool work like the Lasso selection tool in Photoshop, when holding a modifier key a straight line is drawn from one point to another without interrupting the stroke which can be continued again as free hand when the modifier key is released.

when holding a modifier key a straight line is drawn from one point to another without interrupting the stroke which can be continued again as free hand when the modifier key is released.

The DrawScribe plug-in has two tools that are improved versions of the pen and pencil. The pencil replacement tool (Dynamic Sketch) features a straight line mode which works exactly that way (plus you can constrain its angle with Shift).

These are all interesting, if confusing, suggestions, thanks. Maybe I need to clarify what I am trying to do. This first image is of a plan I drew in AutoCADD LT. In full AutoCADD there is a Sketch, or Jitter command that gives

you options to make the lines look like they are draw with pencil, or chalk, or markers. I don't have those controls on my version of the program. So, I was hoping to be able to use Illustrator to convert, nor redraw, the existing lines and curves to look hand drawn. In drafting one uses rulers and Tsquares to keep lines straight, but they often overlap at the ends. The overall effect I wanted was more casual, less rigid, but still drawn using drafting tools.

The second drawing is one I imported as a pdf into Photoshop. Using the brush tool, and the Shift key, I traced over the lines to create the look I wanted. It works, but took several hours to do multiple plans. I was hoping to find a simple filter or command that would take the exisitng lines and apply the effect of the sketchy, hand drawn look without having to redraw everything.

Use "Effect>Distort&Transform>Roughen" to create the look you want for the line. You can add more than one stroke attribute in the "appearance" panel to create a more random look to the line appearance. Here's a picture of the appearance panel that might help:

If you want an "overstroke" appearance, as you've mentioned, you might be able to use ""Effect>Distort&Transform>Transform" and adjust the Horiz/Vert scale, or create an "Art Brush" and assign it to the strokes (brushes can be assigned to any stroke, they do NOT have to be drawn with the brush tool). To create an art brush that extends past the ends of a stroke, build it with it's bounding box shorter than the artwork. The downside is that the "Art Brush" will not be as random as the "Appearance" effects.

I know this is not in the detail you need as a new user of AI. Read all about Appearances, Styles and Brushes, in the online help documentation.